Literature DB >> 19756224

Microwave assisted tandem reactions for the synthesis of 2-hydrazolyl-4-thiazolidinones.

Cecilia Saiz1, Chiara Pizzo, Eduardo Manta, Peter Wipf, S Graciela Mahler.   

Abstract

A tandem method for the synthesis of 2-hydrazolyl-4-thiazolidinones (5) from commercially available materials in a 3 component reaction has been developed. The reaction connects aldehydes, thiosemicarbazides and maleic anhydride, effectively assisted by microwave irradiation. The synthesis of a new type of compound, 2-hydrazolyl-5,5-diphenyl-4-thiazolidinone (7), obtained by treatment of thiosemicarbazone with benzil in basic media is also reported. HOMO/LUMO energies, orbital coefficients and charge distribution were used to explain the proposed reaction mechanism.

Entities:  

Year:  2009        PMID： 19756224      PMCID： PMC2743427          DOI： 10.1016/j.tetlet.2008.12.020

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  12 in total

1.  Domino Reactions in Organic Synthesis.

Authors:  Lutz F. Tietze
Journal:  Chem Rev       Date:  1996-02-01       Impact factor: 60.622

Review 2.  4-thiazolidinone--a biologically active scaffold.

Authors:  Amit Verma; Shailendra K Saraf
Journal:  Eur J Med Chem       Date:  2007-08-06       Impact factor: 6.514

3.  Design, synthesis, and evaluation of 2-aryl-3-heteroaryl-1,3-thiazolidin-4-ones as anti-HIV agents.

Authors:  Ravindra K Rawal; Rajkamal Tripathi; S B Katti; Christophe Pannecouque; Erik De Clercq
Journal:  Bioorg Med Chem       Date:  2006-12-06       Impact factor: 3.641

4.  Dipyridyl thiosemicarbazone chelators with potent and selective antitumor activity form iron complexes with redox activity.

Authors:  Des R Richardson; Philip C Sharpe; David B Lovejoy; Dakshita Senaratne; Danuta S Kalinowski; Mohammad Islam; Paul V Bernhardt
Journal:  J Med Chem       Date:  2006-11-02       Impact factor: 7.446

5.  Synthesis of thiosemicarbazone and 4-thiazolidinone derivatives and their in vitro anti-Toxoplasma gondii activity.

Authors:  Rômulo P Tenório; Cristiane S Carvalho; Carla S Pessanha; José G de Lima; Antônio R de Faria; Antônio J Alves; Edésio J T de Melo; Alexandre J S Góes
Journal:  Bioorg Med Chem Lett       Date:  2005-05-16       Impact factor: 2.823

6.  Chiral 3,3'-(1,2-ethanediyl)-bis[2-(3,4-dimethoxyphenyl)-4-thiazolidinones] with anti-inflammatory activity. Part 11: evaluation of COX-2 selectivity and modelling.

Authors:  M G Vigorita; R Ottanà; F Monforte; R Maccari; M T Monforte; A Trovato; M F Taviano; N Miceli; G De Luca; S Alcaro; F Ortuso
Journal:  Bioorg Med Chem       Date:  2003-03-20       Impact factor: 3.641

7.  Novel aroylhydrazone and thiosemicarbazone iron chelators with anti-malarial activity against chloroquine-resistant and -sensitive parasites.

Authors:  Asikiya Walcourt; Mark Loyevsky; David B Lovejoy; Victor R Gordeuk; Des R Richardson
Journal:  Int J Biochem Cell Biol       Date:  2004-03       Impact factor: 5.085

8.  Synthesis and preliminary evaluation of some pyrazine containing thiazolines and thiazolidinones as antimicrobial agents.

Authors:  Chandrakant G Bonde; Naresh J Gaikwad
Journal:  Bioorg Med Chem       Date:  2004-05-01       Impact factor: 3.641

9.  Synthesis and in vitro evaluation of 5-arylidene-3-hydroxyalkyl-2-phenylimino-4-thiazolidinones with antidegenerative activity on human chondrocyte cultures.

Authors:  Rosaria Ottanà; Rosanna Maccari; Rosella Ciurleo; Maria Gabriella Vigorita; Anna Maria Panico; Venera Cardile; Floriana Garufi; Simone Ronsisvalle
Journal:  Bioorg Med Chem       Date:  2007-09-08       Impact factor: 3.641

10.  Synthesis and structure-activity relationship study of potent trypanocidal thio semicarbazone inhibitors of the trypanosomal cysteine protease cruzain.

Authors:  Xiaohui Du; Chun Guo; Elizabeth Hansell; Patricia S Doyle; Conor R Caffrey; Tod P Holler; James H McKerrow; Fred E Cohen
Journal:  J Med Chem       Date:  2002-06-20       Impact factor: 7.446
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  2 in total

1.  Bisthiazolidines: A Substrate-Mimicking Scaffold as an Inhibitor of the NDM-1 Carbapenemase.

Authors:  Mariano M González; Magda Kosmopoulou; Maria F Mojica; Valerie Castillo; Philip Hinchliffe; Ilaria Pettinati; Jürgen Brem; Christopher J Schofield; Graciela Mahler; Robert A Bonomo; Leticia I Llarrull; James Spencer; Alejandro J Vila
Journal:  ACS Infect Dis       Date:  2015-07-20       Impact factor: 5.084

2.  Regiochemistry of cyclocondensation reactions in the synthesis of polyazaheterocycles.

Authors:  Patrick T Campos; Leticia V Rodrigues; Andrei L Belladona; Caroline R Bender; Juliana S Bitencurt; Fernanda A Rosa; Davi F Back; Helio G Bonacorso; Nilo Zanatta; Clarissa P Frizzo; Marcos A P Martins
Journal:  Beilstein J Org Chem       Date:  2017-02-10       Impact factor: 2.883
  2 in total

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